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375217

Sigma-Aldrich

2-Chloro-4,6-dimethoxy-1,3,5-triazine

97%

Synonym(s):

2,4-Dimethoxy-6-chloro-1,3,5-triazine, 2,4-Dimethoxy-6-chloro-s-triazine, 2-Chloro-4,6-dimethoxy-1,3,5-triazine, 2-Chloro-4,6-dimethoxy-s-triazine, 4,6-Dimethoxy-2-chloro-s-triazine, 6-Chloro-2,4-dimethoxy-s-triazine, CDMT, Chlorodimethoxytriazine

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About This Item

Empirical Formula (Hill Notation):
C5H6ClN3O2
CAS Number:
3140-73-6
Molecular Weight:
175.57
Beilstein:
148988
EC Number:
221-541-0
MDL number:
MFCD00075607
UNSPSC Code:
12352100
PubChem Substance ID:
24863373
NACRES:
NA.22

Assay

97%

form

solid

mp

71-74 °C (lit.)

SMILES string

COc1nc(Cl)nc(OC)n1

InChI

1S/C5H6ClN3O2/c1-10-4-7-3(6)8-5(9-4)11-2/h1-2H3

InChI key

GPIQOFWTZXXOOV-UHFFFAOYSA-N

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General description

2-Chloro-4,6-dimethoxy-1,3,5-triazine is a stable, yet highly reactive, peptide coupling agent. It is reported as useful coupling reagent for the purification of peptides. Catalytic amide-forming reactions of 2-chloro-4,6-dimethoxy-1,3,5-triazine has been reported. Procedure for the preparation of multikilogram quantities of 2-chloro-4,6-dimethoxy-1,3,5-triazine has been reported.

Application

2-Chloro-4,6-dimethoxy-1,3,5-triazine may be used in the following studies:
  • The specific labeling of streptavidin by the modular method for affinity labeling (MoAL).
  • The preparation of bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether, via reaction with 2-hydroxy-4,6-dimethoxy-1,3,5-triazine.
  • The preparation of 2-(4,6-dimethoxy-1,3,5-triazinyl)trialkylammonium salts, via reaction with various tertiary amines.
  • The synthesis of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, via coupling with N-methylmorpholine in THF.
A stable, yet highly reactive, peptide coupling agent.

Signal Word

Danger

Hazard Statements

H314,H317,H411

Hazard Classifications

Aquatic Chronic 2 - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Munetaka Kunishima et al.
Chemical & pharmaceutical bulletin, 61(8), 882-886 (2013-08-02)
Effect of the basic property of reactants (tertiary amine catalysts, a substrate amine, and acid neutralizers) on catalytic dehydrocondensation between a carboxylic acid and an amine by using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) was studied. The reaction yield was affected by the acid-base
An improved procedure for the large scale preparation of 2-chloro-4, 6-dimethoxy-1, 3, 5-triazine.
Cronin JS, et al.
Synthetic Communications, 26(!8), 3491-3494 (1996)
2-Chloro-4, 6-dimethoxy-1, 3, 5-triazine. A new coupling reagent for peptide synthesis.
Kaminski ZJ.
Synthesis, 10, 917-920 (1987)
Konrad Jastrzabek et al.
Chemistry & biodiversity, 10(5), 952-961 (2013-05-18)
Bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether (4) was prepared by treatment of 2-hydroxy-4,6-dimethoxy-1,3,5-triazine with 2-chloro-4,6-dimethoxy-1,3,5-triazine in 61% yield. Ether 4, isoelectronic with pyrocarbonates, was found capable to activate carboxylic acids in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield, under mild reaction conditions, superactive triazine
Munetaka Kunishima et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(49), 15856-15867 (2012-10-13)
The reaction of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) with various nitrogen-containing compounds, particularly tertiary amines (tert-amines), has been studied for the preparation of 2-(4,6-dimethoxy-1,3,5-triazinyl)trialkylammonium salts [DMT-Am(s)]. DMT-Ams derived from aliphatic tert-amines exhibited activity for the dehydrocondensation between a carboxylic acid and an amine
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